I have two policies in our environment to cache the Monterey installer on end users machines first. The second runs a files and processes command based on the machine being queried into a group showing it has the Install macOS Monterey.app present. Once it cache's on the machine, they get queried into the group and makes the second policy available to the user in self service to run the upgrade. The problem I am seeing is that the policy will kick off and run for 30-45 minutes. The machines fan spins up like I would expect during the upgrade process, but the machine will never restart to do the rest. When I check the policy log, it gets all the way to "preparing 106.0% Error: system reboot failed...". At this point the policy shows as completed, but the machine never restarts to finalize the upgrade. Below are a handful of command I have ran that are producing this same result. If I run the update manually on the machine, it gets to the point where I have to physically interact with a window with a restart button for the upgrade to continue. I believe that is where I am getting hung up in my policy and nothing has gotten me past that when trying to trigger it from policy. Has anyone else seen or resolved this issue?
Some of the commands I have attempted with all of the same result. I've tried a ton of other variations and they are all giving me the same behavior as described above also:
sudo /Applications/Install\\ macOS\\ Monterey.app/Contents/Resources/startosinstall --agreetolicense --forcequitapps &...
/Applications/Install\\ macOS\\ Monterey.app/Contents/Resources/startosinstall --agreetolicense --forcequitapps &...
sudo /Applications/Install\\ macOS \\Monterey.app/Contents/Resources/startosinstall --rebootdelay 0 --agreetolicense --nointeraction --forcequitapp...
sudo '/Applications/Install macOS Monterey.app/Contents/Resources/startosinstall' --agreetolicense --nointeraction --forcequitapp..
'/Applications/Install macOS Monterey.app/Contents/Resources/startosinstall' --agreetolicense --nointeraction --forcequitapp..
